Apple is known to be a tough negotiator. How tough, and whether some behaviors cross the line of appropriateness is a question regulators are apparently looking into.

New reports citing “people familiar” suggest the government anti-trust regulators are inquiring about whether Apple’s dealings with music labels have been inappropriate.

On Tuesday, the New York Times reported one of the questions on investigators minds is whether Apple tried to keep the record labels from giving Amazon’s rival music download store exclusive access to some new releases.

Antitrust staff from the DOJ has reportedly contacted several music labels as well as some internet music startups.

The interviews are considered “preliminary” and at this time there is no formal investigation. Still, regulators are clearing keeping a close watch on Apple; an apparent reaction to the dominance the company has established in many of its markets.

The agreement, which was filed on September 25th, will require Amazon to pay $150,000 to the plaintiff’s law firm with KamberEdelson donating its portion of that to charity. (Ed. Update 10/7: the court document is embedded below)

If you were to define irony by example, a book seller going “Big Brother” and secretly deleting your previously purchased copy of 1984 is about as letter perfect as you can get. It’s the kind of thing you cannot script; the truth people deem stranger than fiction. But believe it or not, that’s exactly what happened in mid July.

On July 16th and 17th, Amazon, after recognizing it had sold eBooks it didn’t have proper rights clearances to sell, attempted to fix the problem by dropping a heavy hand on the delete button.

It was a case of now you see it, now you don’t. Last fall, Real Network’s then newly launched DVD copying software platform, RealDVD, went from controversial to contained in the blink of an eye. Just days following the program’s launch, with litigation already filed by both sides, U.S. District Judge Marilyn Patel issued a temporary restraining order blocking all sales of the program pending a broader review of the software’s legality. The program has yet to resurface and now the ongoing copyright litigation is poised to expand.

Designed to enable consumers to create digital to digital archival copies of DVDs, the program was intended to allow owners to store DVDs on a computer for viewing, or backup, without the need to have the disc in the drive.

Bankruptcies are rarely a lender’s friend. They’re a worst case scenario that often means a best outcome of pennies returned on the dollars of investment. Midway Gamesongoing bankruptcy process has been a demonstration in point. Triggered by debt covenants and a sketchy transaction, the proceedings have been riddled with confrontational debate. The rancor’s even spilled over into a counter suit.

Monday, creditors filed suit against the company’s board members, former majority owner, Sumner Redstone, and the buyer of Redstone’s shares, Mark Thomas. The creditors are charging Redstone with fraudulent transfer, and accusing him and others of breaching their fiduciary duties.

Everything stems from Redstone’s firesale giveaway of his Midway holdings in November. Parting with 87% of the company for merely $100k gave Redstone and his affiliated holdings more than $700m in tax losses which created a massive tax write off. That write off, Redstone’s gain, creditors argue, helped shore up the finances at Redstone’s National Amusements but put Midway into a tailspin.

“The transaction caused Midway irretrievably to lose the ability to take advantage of its valuable accumulated net operating losses and other tax assets,” creditors say.

The Boston Globe paper lost $50m in 2008 and was poised to lose another $85m this year if it continued on the same path. Looking to slow the bleeding, the Times Co. wanted at least $20m in concessionary cutbacks, and other contractual concessions (including the elimination of some lifetime job guarantees).

With high level soundbytes, the deal was billed as an achievement. Richard Sarnoff, Chairman of the Association of American Publishers, characterized it as a “win for everyone.” All that was necessary to go forward was court approval and that was considered a formality scheduled for May 5th. Turns out, that timetable was a little optimistic.

On Tuesday, responding to objections made by a number of authors, Judge Denny Chin of the U.S. District Court for the Southern District of New York extended the settlement’s review period until September 4th and scheduled a final fairness hearing for October 7th, 2009.

The authors had expressed concern that the original schedule didn’t provide enough time to review the complex settlement’s terms. They requested six more months. Google and the Author’s Guild, the core parties of the settlement, thought a sixty day extension should be enough. The judge split the difference.